Early in 1939 Robert Charles Benchley—Phillips Exeter Academy, 1908; Harvard, 1912—put on a paper hat and hoisted himself up onto a set of phony telephone wires strung between mock utility poles on a Metro-Goldwyn-Mayer sound stage in Hollywood. He was filming one of the ten-minute comedies that were eroding his self-respect while increasing his fame and income.

In this film, Dark Magic , Benchley was portraying a clumsy father who fiddles with a toy magic kit he bought his son and disappears in a puff of smoke. He is next seen balanced precariously on the telephone lines, still engrossed in the toy’s instructions. Benchley lay down on his stomach, stretching his six-foot, two-hundred-pound frame across the wires, and brooded there uncomfortably while technicians adjusted their lights and camera. His wife of twenty-five years, Gertrude Darling Benchley, happened I to be on the set watching. “Remember how good in Latin I was in school?” Benchley asked her. “Well, look where it got me.”

In many ways Robert Benchley was, as the film historian Robert Reddine wrote, “a by now familiar figure: the professional humorist who at heart is a deeply troubled man. …” But Benchley was also a man of immensely ingratiating, almost indefinable charm, whose self-effacing humor in print, on film, and in person enthralled and influenced his contemporaries. Forty years after his death, he is still admired, envied, and emulated by those who would make us laugh.

“I’ve got most of my Benchley books up in Nantucket,” says Russell Baker, “and if I’m up there working on a column, sometimes I’ll pick [one] off the shelf and see if there is anything in it I can steal.”

“Benchley was one of my role models when I was a kid,” says Art Buchwald. “When I grew up, I stopped reading Benchley because he had thought of every good idea before I did … [and] he inhibited me.”

“Bob Benchley is bone china to my Melmac,” says Erma Bombeck. “If he were alive, I’d be sitting at his right hand making notes.”

Benchley was a leading drama critic in New York for more than twenty years and simultaneously the star of a highly successful series of comedy films, one of which— How to Sleep —received the Academy Award as the best short subject of 1935. He also appeared in dozens of mostly forgettable feature films as a supporting actor, often adding the only wisp of class to the movie. In a thirty-year writing career he produced hundreds of comic essays still prized for their elegance and economy. He also was the paterfamilias of a clan of writers, the latest of whom is his grandson, Peter Benchley, author of Jaws, The Deep , and other books.

Robert E. Sherwood, a longtime Benchley friend and Pulitzer Prize-winning playwright, once wrote that Benchley’s life “represented some of the strangest reversals of moods and habits I have ever observed in one human being.” Benchley described himself as a “confused liberal.” He was a registered Republican who often voted Democratic, a former social worker who fought injustice and took part in the effort to win a new trial for Sacco and Vanzetti, and a devotee of the Queen Anne period in English history who yearned to write scholarly books. He was a frugal homebody and ardent prohibitionist who became a perpetually absent husband and father, a generous spendthrift, and a notoriously rollicking imbiber with a remarkable talent for friendship.

Benchley never could resolve the inner conflict between his low opinion of the humorous writing he did and the enthusiasm with which he wrote it—or with the financial rewards it brought. “He felt that he had burned himself out on the mass production of trivia when he should have been doing something better, and he knew that his fame was more because of the movies than because of his writing …,” wrote the late Nathaniel Benchley in his biography of his father. Robert Benchley’s dilemma, according to his son, was that “he didn’t really want to be funny … [but] the only way he could make money was as a comedian.” Throughout his life Benchley was plagued by a “New England conscience that tortured him like a hot iron, and made him want to shake loose from a whole way of life”—the one he led in New York and Hollywood. On the other hand, he was extremely adept at outwitting that conscience, having a good time, and seeing to it that all in his company enjoyed themselves too.

Benchley’s antecedents in humor were such literate observers of human folly as Oliver Wendell Holmes, author of “The Autocrat of the Breakfast-Table,” and George Ade, the Hoosier whose Fables in Slang enriched the language; Heywood Broun; Ring Lardner; and F.P.A. (Franklin P. Adams), whose newspaper column, “The Conning Tower,” and other writings, said Benchley, made “it possible for us to admit our learning and still be held honorable men.”

Benchley’s humor reflected all these veins. He could be a deft parodist, a satirist, a writer of glorious nonsense, and perhaps most memorably, a woebegone chronicler of his own bumbling inadequacies.

“It may be that my fingers were frozen when I was a very small child and have never quite thawed out, or it may be that I just become panicky at having a man look at me through a little window, but, whatever the cause, I am physically unable to pick up change which has been shoved out at me by a man at a ticket-booth.

“I can scoop up change like lightning from a store-counter… but let me stand in front of a ticket-window in a theater lobby or a railroad station, with a line of people behind me, and a boy with a magnet could pick up a mound of iron-filings one by one quicker than it takes me to garner 20 cents in change.”

Benchley was helpless at driving a car, couldn’t comprehend machinery of any sort, and railed at the impossibility of opening such things as a package of mints. “It may be a perfectly dandy wrapper, air-tight, water-tight and germproof, but if the buyer has to send it to a garage to get it off, something is wrong somewhere.” Rather than struggling with the recalcitrant ice trays in his refrigerator, he would send out for a bag of ice and patiently await its arrival. He battled all inanimate objects—and lost.

“The hundred and one little bits of wood and metal that go to make up the impedimenta of our daily life—the shoes and pins, the picture hooks and door keys, the bits of fluff and sheets of newspaper—each and every one [has] just as much vicious ill will toward me personally as the meanest footpad who roams the streets. … I can’t fight these boys. They’ve got me licked.”

According to his son Nathaniel, this was no exaggeration for comic effect. It was the truth. It is also what made Benchley’s movie portrayals of ineptitude so wonderfully natural and his essays about his failings—and his reactions to modern living—so appealing.

Benchley did not try to define why he was funny. In fact, he agreed with E. B. White that humor “can be dissected, as a frog can, but the thing dies in the process.” As a theater critic Benchley liked all kinds of comedy, from the subtle, understated manner of Will Rogers, the last great homespun wit, to the antics of the Marx Brothers, Ed Wynn, and Jimmy Durante. He was extravagant in his praise for both styles, but personally he seems to have preferred the quiet, straightfaced approach in most of what he wrote and performed. He often insisted that he didn’t have any style at all. “I don’t know enough words to have a style; I know, at most, fifteen adjectives.”

Benchley was singularly unimpressed with his own efforts. He believed, correctly, that he was no actor, in the sense that he was unable to duplicate his performances and employed none of the theatrical tricks of the trade when appearing before the camera. And although he wrote with slow, agonizing precision, he felt that none of his essays qualified him to claim that he was a writer. It took him, he said, “fifteen years to discover that I had no talent for writing, but I couldn’t give it up because by that time I was too famous.” But in fact he had as much to do with creating the general tone of The New Yorker as any of its early staff.

Benchley was born in Worcester, Massachusetts, on September 15, 1889, the son of Charles H. Benchley, a mildmannered nonpartisan aide to a dozen Worcester mayors, and Jane Moran Benchley, known as Jennie to the family, a stern prohibitionist who nonetheless had a sharp sense of humor and could readily laugh at herself.

Both of Benchley’s parents could trace their American lineage to before the Revolution, and Benchley’s paternal grandfather, Henry W. Benchley, served as a member of the Massachusetts Senate and as lieutenant governor of the state from 1856 to 1858. He helped found the Republican party in the eastern United States and was imprisoned in Texas during the Civil War for setting up a branch of the Underground Railroad there. His wife, Julia, was regarded in Worcester as a bit of an eccentric, a judgment that was posthumously reinforced when she willed her head to the local hospital so medical students could examine it.

Benchley’s parents were married in 1874, and their first son, Edmund Nathaniel, was born two years later. He was the focus of his parents’ fierce affection for thirteen years before they suddenly surprised themselves by producing Robert. Edmund doted on his baby brother, who returned the devotion. When Robert was in his first year of school, he was assigned the task of memorizing a poem of his own choosing and went to his older brother for help. Edmund solemnly taught him:

My mother-in-law has lately died; For her my heart doth yearn. I know she’s with the angels now ’Cause she’s too tough to burn.

Edmund, a handsome, dashing figure, received a commission to West Point in 1894. In 1898 his class was graduated early in order to go off to the SpanishAmerican War. During a skirmish in Cuba on July 1, Edmund was shot through the heart and killed. Word of his death reached Worcester on July 4, just as the town was about to erupt in its traditional Independence Day festivities. His mother went into shock, and in her hysteria she blurted, “Oh, why couldn’t it have been Robert?” Soon everyone in town, including Robert’s classmates, knew what she had said.

She spent the rest of Robert’s childhood—indeed, the rest of her life—trying to atone for those words. She catered to his every need and even tied his shoes for him each morning until he was old enough to go to high school. She also added a fanatic pacifism to her prohibitionism, and both were bulwarks of Benchley’s own philosophy. Although he later enthusiastically took up drinking, he remained antiwar, writing in the mid-1920s of “five million youths, cheered on by a hundred million elders with fallen arches, marching out to give their arms and legs and lives for Something to Be Determined Later.”

Edmund had been secretly engaged to Lillian Duryea, heiress to the fortunes of a prosperous starch business. She practically adopted Robert, eventually placing him in Phillips Exeter Academy at her own expense.

At Exeter, Robert was judged a fine, though not superior, student. Once he was assigned to write an essay on something “practical,” so he went to the local mortician and prepared a thorough, precise paper on how to embalm a body. His queasy but impressed teacher gave him an A.

It was also Lillian who insisted that Robert go to Harvard, and she lent him the money for tuition. Benchley’s contemporaries there included Walter Lippmann and John Reed. Years later Benchley recalled Reed as a radical who “smiled now and then and even cracked jokes, and did not always enter the room as if … [he] were the man coming to take away the piano.” Benchley became president of the Harvard Lampoon , the student humor magazine, on which he worked with Frederick Lewis Allen, a future editor in chief of Harper’s Magazine ; Henry Holt, Jr., who later published some of Benchley’s books; and Gluyas Williams, whose incomparable drawings illustrated them.

Benchley’s philosophy of higher education was one that has been admired and followed by many undergraduates. “My college education was no haphazard affair,” he later wrote. “My courses were all selected with a very definite aim in view, with a serious purpose in mind: No classes before 11 A.M. or after 2:30 P.M. and nothing on Saturday. … On that rock was my education built.” He claimed that such a regimen enabled him to take courses on the social life of minor sixteenth-century poets, Russian taxation systems before Catherine the Great, and North American glacial deposits.

As he had in grammar school, in high school, and at Exeter, Benchley became involved in theatrical activities at Harvard, writing and acting in several productions of the Hasty Pudding Club. He also became renowned among his fellow students—and even around Boston—for delivering mock lectures and travelogues, perhaps the most memorable of which was entitled “Through the Alimentary Canal with Gun and Camera.”

Because he failed a course in international law by responding incorrectly to an exam question about a fisheries dispute (he looked at it from the point of view of the fish), Benchley did not get his degree with his class and later had to take makeup courses. But as president of the Lampoon he was still called upon to deliver the traditionally humorous Ivy Oration at commencement. His adlibbed parody of academic and political rhetoric, delivered to a huge audience that had suffered through two days of ponderous speeches, was greeted with wild enthusiasm.

His success as a college humorist was so great that the editor of the Boston Journal offered him a job writing a daily humor column. Benchley turned it down with the observation that he didn’t want to have to be funny every day. Shortly afterward he moved to New York City, where he got a job writing advertising copy for the Curtis Publishing Company. He had only modest luck extolling the benefits of advertising in Curtis publications, and his career there came to an abrupt end early in 1914, not long after he had attended the company’s annual dinner wearing a red wig, a false beard, and eyeglasses, passing himself off as a “Mr. Constantine,” president of a Seattle advertising agency. His immediate superior had approved of the prank and seated Benchley next to none other than Cyrus H. K. Curtis himself. When called upon to speak, Benchley delivered a furious denunciation of the Curtis Publishing Company, so enraging Curtis that the publisher had to be restrained from attacking him. As a finale, Benchley doffed his disguise and sang a chorus of “Heaven Will Protect the Working Girl.” The audience had been so gulled by Benchley’s performance that only scattered applause and laughter greeted it, and Curtis grumbled that the hoax seemed “funny now. But it wasn’t funny five minutes ago.” In a matter of weeks Benchley was looking for a job. Years later he remarked that the company gave him “plenty of time to get my hat and coat, and they advised me to stay out of advertising, because I was too tall.… Curtis stayed in Philadelphia in its small way and I went elsewhere.”

The “elsewhere” turned out to be Boston, where the Russell Paper Company hired him to be the “welfare secretary” for its paper-mill employees, organizing company bowling matches and clambakes.

During this period Benchley submitted some brief humorous essays to Frank Crowninshield, then an editor of The Century magazine, who rejected them but urged him to write more. This encouragement and his employment with the paper company persuaded Benchley that he was financially solvent enough to marry Gertrude Darling, whom he had known since they were in grammar school. They were married on June 6,1914, and the following October his first commercially published article appeared in Vanity Fair , of which Crowninshield had just become the editor. The article spoofed the titles then favored for popular novels and suggested as a suitable candidate: “No Matter from What Angle You Look at It, Alice Brookhausen Was a Girl Whom You Would Hesitate to Invite into Your Own Home.”

Benchley’s comic speeches were still fondly remembered in Boston, and he was asked to address the Harvard Club’s dinner honoring the university’s undefeated football team, which had just whipped Yale 36 to 0. He and some friends managed to cajole a local Chinese merchant into wearing a dress suit and impersonating a “Professor Soong” of the Imperial University of China, whose address on “Chinese football” would be “translated” by Benchley. The merchant rattled off a stream of obscenities and invective in Chinese, while the unwary audience (all except for one Chinese alumnus) waited for Benchley’s explanation of what was being said.

Yale’s coach Frank Hinkey had introduced the lateral pass to the game that year, certainly without success against Harvard, and Benchley proceeded to tell the audience that the play called the kaew chung , or lateral pass, was actually an ancient Chinese invention, “but as in no instance was it ever known to gain over three yards, and that in the wrong direction, it was abandoned in the year 720.” Benchley then asked the “professor” what he thought Harvard needed to continue its splendid record on the gridiron, and after the Chinese merchant had cursed for at least five minutes, Benchley paused, turned to his listeners, and interpreted: “He says, ‘Hinkey.’ ”

The whole performance received considerable coverage in the local press and caused one writer to dub Benchley “the greatest humorist of all time at Harvard.” He subsequently was invited to attend every Harvard Club dinner and even received an invitation to address the Harvard Club in Chicago. The university’s president, Abbott Lawrence Lowell, also was scheduled to speak to the Chicago alumni but insisted that he be placed on the bill before Benchley, knowing that to follow him would be disastrous.

Shortly after Benchley’s much acclaimed appearance with “Professor Soong,” he secretly was invited to address Boston’s Wardroom Club, a group of Navy officers. There he impersonated Stanton Abbott, private secretary to Josephus Daniels, the teetotaling secretary of the Navy who wanted to ban liquor from the fleet. Benchley told the officers that not only was it the secretary’s intention to expunge “even the memory of vile spirits from our jolly jack tars,” but also, in an effort to apply a “single standard of morality” to officers and enlisted men, officers henceforth would be required to undergo the same “physical examination and certain prophylactic treatment” that was administered to crewmen following liberty. It only gradually dawned on his listeners that they were being snookered.

As gratifying as these public appearances were, they did little for Benchley’s bank account. The paper company for which he was working also was having financial difficulties, and a week after his first son, Nathaniel, was born in November 1915, the firm told Benchley that “the boys had had enough clams” and his services as welfare secretary were no longer required.

Franklin P. Adams had earlier offered him a thirty-five-dollar-a-week job as a reporter on the New York Tribune . While Benchley wasn’t especially interested in becoming a reporter, he now was in desperate need of a job, and he accepted the offer. On January 1, 1916, Benchley arrived at the Tribune to become, he later wrote, the “worst reporter, even for my age, in New York.”

Benchley was rescued from the newspaper’s city room by being transferred to its new supplement, the Tribune Magazine , and he began to relish his association not just with Adams but with other colleagues, such as the sportswriter Heywood Broun, the drama editor George S. Kaufman, and the music critic Deems Taylor. On the Magazine Benchley wrote a feature story and a book review each week, and he also began turning out parodies of popularized science articles, exploring such subjects as “Do Jelly Fish Suffer Embarrassment?”

Benchley continued his happy employment with the Tribune until the Magazine was abruptly discontinued in May 1917. Needing a full-time job, he spent twelve miserable weeks working as a press agent for the irascible William A. Brady, a Broadway producer to whom Benchley took an immediate dislike. He also continued producing free-lance pieces, drawing on his experiences as a harried young suburbanite and father. He wrote of the perils of trying to operate a home furnace and of traveling with an infant: “In America there are two classes of travel—first class, and with children. Traveling with children corresponds roughly to traveling third class in Bulgaria. …

“Those who have taken a very small baby on a train maintain that this ranks as pleasure along with having a nerve killed. On the other hand, those whose wee companions are in the romping stage, simply laugh at the claims of the first group. Sometimes you will find a man who has both an infant and a romper with him. Such a citizen should receive a salute of twenty-one guns every time he enters the city and should be allowed to wear the insignia of the Pater Dolorosa, giving him the right to solicit alms on the cathedral steps.”

Fortunately, Benchley was soon asked to come back to the New York Tribune by Ernest Gruening, an old friend who was now managing editor. The job was as a seventy-five-dollar-a-week editor of the Tribune Graphic , a twelve-page prototype of the Sunday rotogravure section. The job, his fourth within a year, would last all of ten weeks.

After Benchley had been at the Tribune Graphic for a month, he and Gruening decided to use the section to make a plea for racial tolerance. They juxtaposed a photograph of black troops being awarded medals in France with a picture of a lynching in Georgia. Minutes after the section had rolled off the presses, they were summoned by management and ordered to remove such “pro-German” propaganda from the paper. A month later Gruening was fired. He was told that rumors of his German sympathies (apparently fostered by his Teutonic-sounding name) made his presence on the paper “embarrassing.” Infuriated, Benchley immediately wrote out his resignation, addressing it to Ogden Reid, the publisher, and to two of the more senior editors. “I haven’t the slightest idea who is boss on this sheet, so I am sending this resignation to the three whom I suspect,” he wrote. A few months later, shortly before the birth of his second son, Robert, Jr., Benchley was offered the job of managing editor of Vanity Fair , where he became friends with Robert E. Sherwood, the twenty-three-year-old drama editor, and Dorothy Parker, the twenty-six-year-old drama critic. Sherwood stood six feet seven inches tall. Parker may have topped five feet. Benchley was six feet tall. The three became inseparable, and when they walked down the street together, they looked, said Nathaniel Benchley, “like a walking pipe organ.” The trio enjoyed baiting management. Once a directive came down forbidding employees to discuss their salaries. Benchley, Sherwood, and Parker responded by printing their salaries on cardboard signs, which they hung around their necks.

Their jocular stay at the elegant Vanity Fair came to an end in January 1920 when Parker wrote an unflattering review of a performance by Billie Burke, known to a later generation as the good witch Glinda in The Wizard of Oz but then the wife of the powerful impresario Florenz Ziegfeld. Ziegfeld complained loudly and long to Vanity Fair ’s management, and she was sacked. Benchley and Sherwood responded by quitting. It was, the critic John Mason Brown wrote years later, a characteristic move for Benchley to make: “spirited, generous and quixotic.… He had a family to support, too little money, too many debts, and now not even a regular job.” But he had been without a job before and always seemed to manage.

Benchley and Parker briefly rented a tiny, triangular office on the third floor of the Metropolitan Opera House studios. It was so small, Benchley later said, that “one cubic foot less of space and it would have constituted adultery.” Benchley wrote advertising copy on a free-lance basis and without enthusiasm, but he also arranged to do a regular column called “Books and Other Things” for the New York World , with the “other things” in the title enabling him to write parodies, satires, and commentary about whatever he saw fit. In April the post of drama critic opened on Life , a comic weekly for which Benchley had longed to work. (When it folded a decade and a half later, Henry R. Luce bought the rights to its name for his new picture magazine.) Benchley was hired and at last settled into a job he would hold for the next nine years. It also would change the way he lived and permanently alter his relationship with his family.

A month after he went to work for Life , Benchley purchased a house in the suburb of Scarsdale. In the early 1920s six to nine new plays opened each week during the theater season, and Benchley sometimes dashed to three different openings in a single night. He rarely got home for dinner more than once a week, and the commuting wore him out. Eventually he rented an apartment in the city and went home only on weekends and occasionally only on Sunday. His wife and sons “became the commuters,” Nathaniel Benchley later wrote, traveling to his apartment in New York and later to his bungalow in Hollywood to see him. That remained the case for the rest of Benchley’s life. Although the outward relationship between Benchley and his wife remained cordial, and they sometimes shared vacations and always spent the Thanksgiving and Christmas holidays together, it is clear they grew apart. Late in life Gertrude Benchley told an interviewer, “I had him so early, and I knew what his possibilities were and that I had to share him—so I did.” She remained a proper, slightly prim New Englander, uninterested in the glitter of Broadway or Hollywood or their inhabitants, while he became a bon vivant of epic proportions, with a seemingly unending supply of boon companions and several aspiring actresses as girl friends. He may have been .tormented by pangs of conscience periodically, but nonetheless he began to lead what Wolcott Gibbs, then on the staff of The New Yorker , called “one of the most insanely complicated private lives of our day. …”

He also began to drink. Though he had originally rejoiced over the adoption of prohibition, Benchley now was constantly in the company of a hard- drinking crowd, and at the age of thirtytwo, he decided to try liquor. His first glass of rye whiskey “came as a nostalgic, jarring shock,” his son later wrote. Its smell reminded Benchley of the “personal bouquet” of a long-dead relative. “My God,” he said. “It’s Uncle Albert.” At last Benchley realized what his uncle had been up to during the frequent trips he made to the family barn back in Worcester.

In time Benchley’s drinking surely equaled and probably outstripped his Uncle Albert’s. He would begin downing cocktails at five in the afternoon and frequently continued drinking for the next ten hours. His capacity “was one of the marvels of the age,” a biographer wrote, and he was rarely seen to be overtly inebriated. He appears to have become a sort of polite alcoholic—always courteous, ever convivial, frequently jolly, but forever with glass in hand. “He was a very amusing drunk,” recalls Al Hirschfeld, the New York Times theatrical caricaturist for the past sixty years and a habitué of many of the speakeasies Benchley patronized. “Sometimes that’s the penalty you pay when you become a character. It happened to Dylan Thomas, you know, and it’s one of those things. People just expect you to behave like a drunk, and so I suppose you live up to your mythology.”

In addition to his work as drama critic for Life , Benchley continued to write comic essays and oversaw the production of a spectacularly successful “Burlesque Issue” of the magazine that featured spoofs of other publications. In a section parodying the New York Daily News , he printed a bird’s-eye photo of a happy crowd surrounding Britain’s gilded royal coach and captioned it: “Convention-Crazed Dentists Parade Through Streets of London Dragging Largest Gold Tooth in the World.”

One of Benchley’s duties as drama critic was to write a brief description of each play on Broadway for the magazine’s “The Confidential Guide,” a forerunner of the “Goings On About Town” section in The New Yorker of today. He was bedeviled by the inexplicable five-year run of Abie’s Irish Rose , a comedy about a Jewish boy who marries an Irish girl. It premiered in May 1922 to resounding raspberries from all the critics, Benchley included, but from June 1922 to November 1927 he had to come up with something new to say about it every week. His comments included: “People laugh at this every night, which explains why democracy will never be a success,” and “Flying fish are sometimes seen at as great a height as fifteen feet.” He even ran a mock contest for the best “Confidential Guide” comment on the play and awarded the laurel to “Mr. Arthur Marx,” alias Harpo, who offered, “No worse than a bad cold.”

In general, however, Benchley was an indulgent critic, both at Life and later for The New Yorker , where he worked from 1929 to 1940. His play reviews often were similar in style to his essays. He depicted himself as a “basically sensible fellow who happened to be sizing up plays instead of selling suits or running an office,” wrote one of his biographers, Norris Yates. “I always know that a play is clumsily written,” Benchley said in one review, “if I can detect passages in it that I myself might have done.” He felt an ideal audience was one that “responds to thrills and to sentimentality, but retains … [its] critical faculty,” and he scorned the sort of theatergoer who applauds reflexively for such things as a “musical ensemble in which the entire company raises its arms and wiggles its fingers.” His reviews, a former colleague at The New Yorker wrote after his death, “reflected a complete personality, genial, sensitive, informed, too mature and tolerant to care about the easy, rather discreditable reputation for wit that can come from hasty and intemperate ridicule. It was a weapon he didn’t need, anyway; his disapproval was all the more effective because it always seemed clear that his kind heart was far more anxious to admire and praise.”

Al Hirschfeld, who was a frequent firstnighter with Benchley, believes he was not only a superb critic but a wonderfully unpretentious one. “He was the last theater critic who really laughed out loud in the theater,” Hirschfeld recalls. “He would applaud like mad and laugh and knock himself out. You could hear him all over the house. He was very outgoing. You know, critics since then don’t applaud at all. They know they’re being watched. But he was completely unaware of being a critic.”

Benchley also was unusually concerned about the actors and actresses whose performances he reviewed, and he fretted over the possible harm a negative notice from him could do to their careers. In the early years of the Depression he donated 10 percent of the royalties from one of his books to the Actors’ Unemployment Relief Fund.

Benchley’s empathy for actors was enhanced when he joined their ranks, at first with reluctance and then with increasing frequency. In 1922 the writers, critics, and performers who frequented New York’s Algonquin Hotel decided to put on a one-night, invitation-only review, which they called No, Sirree! Benchley’s contribution was an eightminute, ad-libbed parody of the numbing speakers he had covered as a young reporter. As he later recounted, the moment he began his offhand performance of what became known as “The Treasurer’s Report,” his “entire life changed its course.”

Irving Berlin and producer Sam Harris were in the audience, and they loved Benchley’s portrayal of a befuddled assistant treasurer trying vainly to fill in for an organization’s regular bookkeeper. They offered him a spot in their next Music Box Revue . Benchley had reservations about being a drama critic who also acted, so he asked for the outrageous sum of five hundred dollars a week, thinking that would cool Berlin and Harris’s enthusiasm. Instead, he got it. The following year he had to perform his little speech on Broadway for nine months, squeezing his appearances onstage in between his rounds of the theaters for Life . He then spent another ten weeks touring the Keith vaudeville circuit during the summer, when there were no new shows to review. Benchley later wrote that no one ever became as sick of anything as he was of “The Treasurer’s Report,” but performing it increased his income enormously, established him as a celebrity, and represented, in a way, a new kind of comedy: a monologue completely devoid of gags, that depended on deft characterization for its humor.

Benchley’s increasing fame brought more opportunities. He swallowed his distaste for the “papier mâché hills of Hollywoodland” and what he considered “the country’s most frothy and inconsequential citizens” and went west to write subtitles for a film starring Raymond Griffith, an elegant, top-hatted comedian. He also began writing “The Wayward Press” column for The New Yorker , analyzing the city’s newspapers under the pseudonym Guy Fawkes; started the drama department for The Bookman ; continued his play reviewing for Life ; and in January 1928 unintentionally launched his own film career by agreeing to make a movie version of “The Treasurer’s Report.” It was the first commercially successful, all-talking picture. (Al Jolson’s The Jazz Singer had little spoken dialogue and was largely a musical film with subtitles.)

Benchley went to the Fox movie company’s studios in Astoria, Long Island, and shot the ten-minute film in one day, adding the presence of a “chairman” to introduce him, reciting the monologue as he had done hundreds of times before, and supplying a few more pieces of comic business. When the film was released four months later, it was an immediate success, earning a whopping $165,000 in its first year. (It had cost less than $16,000 to make.) Not surprisingly he was persuaded to make a second film, The Sex Life of the Polyp , in which he combined portions of three Vanity Fair articles—“The Social Life of the Newt,” “Do Insects Think?” and “Polyp with a Past”—and posed as a scientist to deliver a patently absurd lecture. He then made three more films for Fox, basically reworking material he already had written on tending a furnace, learning to drive, gardening, and bridge playing.

As a devotee of the theater, however, Benchley disliked, even feared, talking pictures, and he resisted further film blandishments—at least for a few years. But the movie work wasn’t as taxing as his writing, and the money was irresistible. He could earn fifteen hundred dollars a week in Hollywood compared with the three hundred dollars a week he got from The New Yorker . He retained his scorn for the motion-picture medium for the rest of his life—“good actors in a good play can make a monkey out of the movies,” he wrote in 1938—but as his activities as a motion-picture performer grew, he gradually withered as a writer. He spent up to six months a year in Hollywood, turning out light dialogue for feature films, appearing in some of them, making his own comedy shorts, and cavorting with the sort of people he once had called frothy but now considered close friends.

Benchley became a cross-country commuter. In New York he lived amid a spectacular clutter of gewgaws, exotica, and junk crammed into a two-room apartment in the Royalton Hotel, across the street from the Algonquin. His apartment became “as famous as, and in some ways resembled, the Smithsonian Institution,” Nathaniel Benchley wrote. Its controlling motif was Victorian, with three impressive portraits of the old queen hung between the windows. The color scheme was primarily red, but the main room contained a blue couch that Benchley called the track. Whenever he got ready to lie down on it for a nap, he would say, “Well, I guess I’ll do a couple of laps around the track.”

The apartment’s minuscule foyer was stuffed with trunks, old newspapers and magazines, bound volumes of The New Yorker , canes, coats, a sword, and even a deer skull. One five-foot bookshelf contained nothing but books that had been collected for their titles, such as Talks on Manure, The Culture and Diseases of the Sweet Potato, Success with Small Fruits, Bicycling for Ladies, and Forty Thousand Sublime and Beautiful Thoughts . Another bookcase was adorned with hideous little carvings made out of roots, miniature geese, and water-filled glass globes that could be shaken to whip up small snowstorms inside. Sandwiched in between these trinkets were Benchley’s extensive collection of books about the Queen Anne period and first editions of the works of his friends Scott Fitzgerald and Ernest Hemingway. “Old Ernie” occasionally stayed at Benchley’s New York apartment and once mischievously wrote scatalogical inscriptions in several of his books. In A Farewell to Arms he patiently filled in all the blank spaces that the publisher had delicately substituted for the rawer words in the manuscript. He then noted on the flyleaf: “Corrected edition with filled-in blanks. Very valuable—sell quick.” Also part of Benchley’s fifteenhundred-volume library—but stashed in the closet—was a collection of scholarly books, some of them in German, that he did not want people to know he read. He was afraid of being considered pretentious, and sometimes he would hide the true nature of a book he was reading by covering it with the dust jacket from a murder mystery.

Benchley was a nocturnal person, famed for his marathon excursions around Manhattan, where he seemed to know all of the out-of-the-way taverns that were distinguished principally for the fact that they stayed open all night. Sometimes his small-hour prowling ended up at Grant’s Tomb, where a few of his friends once surreptitiously spotted him placing a note in a milk bottle by the steps leading up to the tomb. After he had left, they checked the note, which read: “One milk, no cream. [Signed] U.S. Grant.” He also was a frequenter of the bordello maintained by the celebrated Polly Adler, but one biographer insists that he used it only as a place to get some sleep or the quiet he needed to write.

Benchley managed to do a prodigious amount of work despite his frenetic social life. In 1933 he began writing a thriceweekly newspaper column for Hearst’s King Features Syndicate and continued it for three years; from 1938 to 1940 he hosted a popular variety show on radio while also making numerous guest appearances on other programs; he published twelve collections of his essays; made forty-eight movie shorts, and either wrote dialogue for or appeared in forty-seven feature films.

All the while, Benchley continued his association with The New Yorker , but writing became an agony for him, and his work for the magazine began to suffer. By 1940 the editor, Harold Ross, had to dispatch an assistant, St. Clair McKelway, to tell Benchley that Wolcott Gibbs would be replacing him as drama critic. McKelway met Benchley for cocktails but couldn’t bring himself to deliver the ill tidings. Typically, Benchley knew precisely what was on McKelway’s mind and told him he understood perfectly. “It was his knack to take other people’s side, especially when they were in trouble,” wrote Brendan Gill in his book about The New Yorker . In December 1943 Benchley gave up writing altogether, making a formal announcement that he was going to concentrate on movie and radio work instead, believing that few humorists were funny after they had reached the age of fifty.

Beneath the surface of Benchley’s almost perpetual bonhomie was a profound depression over the course his career had taken. When he would enter the Harvard Club in New York with the announcer from his radio show, he repeatedly responded to the happy greetings of friends with a falsely cheery “I’m fine, just hurting inside.” Shortly before he abandoned writing, he was attending a party in Hollywood to celebrate the second of Robert Sherwood’s Pulitzer Prizes for drama. Fitzgerald and Dorothy Parker were also there. Late in the evening Benchley began muttering, “Those eyes—I can’t stand those eyes looking at me!” He began backing away from Sherwood, and everyone thought he was about to make a joke. It was no joke. Benchley pointed at Sherwood and said: “He’s looking at me and thinking of how he knew me when I was going to be a great writer. …And he’s thinking now look at what I am!” Sherwood later told Benchley’s son that he probably had, unhappily, been thinking along just such lines.

“[My father] had a theory that everyone tends to become the type of person he hates most,” Nathaniel Benchley wrote, “and when he gave up writing he gave up the one thing in which he had honest pride.”

In October 1945 Benchley had a complete physical checkup on the West Coast. His astonishing constitution and stamina appeared undiminished, but actually they weren’t. Late in November, shortly after returning to New York, he began to suffer a series of nosebleeds and finally had one that wouldn’t stop. He was taken to the Columbia-Presbyterian Medical Center, toting along a book of philosophical essays including one entitled “Am I Thinking?” He had jotted in the margin, “ NO . (and supposing you were?)” At the hospital he began hemorrhaging, lapsed into a coma, and died of a cerebral hemorrhage on November 21. He was fifty-six.

When his friend George Ade had died the year before, Benchley said, “When a great humorist dies, everybody should go to a place where there is laughter and drink to his memory until the lights go out.” Hundreds of Benchley’s friends did just that, gathering at Romanoff’s in Beverly Hills and “21” in New York, where a small plaque beside his favorite table still honors his memory, reading “Robert Benchley, His Corner, 1889–1945.”

Ironically, the movies of which Benchley thought so little may be his most enduring work. James Thurber, not generally considered a sentimental man, wrote four years after Benchley died that he had left a “rich legacy of humor, comedy, satire, parody and criticism—all rolled into one in those … magnificent movie shorts.” Critics missed the point when they disparaged Benchley’s short essays, Thurber wrote, underestimating the tremendous skill that was required to create these “distinguished contributions to the fine art of comic brevity.” Critics also made a mistake when they tried to classify Benchley’s writing or place him in a “school” of humor. “To most of us,” Thurber wrote, “he stands alone, in a great good place all his own.” One of Benchley’s friends had remarked upon his death, “They’re going to have to stay up late in heaven now,” and Thurber wistfully agreed: “Yes, they’re staying up late, I know, and, what is more, they must be having the time of their infinities. Lucky angels.”